GB1142484A - Improvements in or relating to steroids and the manufacture thereof - Google Patents
Improvements in or relating to steroids and the manufacture thereofInfo
- Publication number
- GB1142484A GB1142484A GB12857/66A GB1285766A GB1142484A GB 1142484 A GB1142484 A GB 1142484A GB 12857/66 A GB12857/66 A GB 12857/66A GB 1285766 A GB1285766 A GB 1285766A GB 1142484 A GB1142484 A GB 1142484A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- keto
- hydroxy
- hydrogen
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J53/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by condensation with a carbocyclic rings or by formation of an additional ring by means of a direct link between two ring carbon atoms, including carboxyclic rings fused to the cyclopenta(a)hydrophenanthrene skeleton are included in this class
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,142,484. Steroids. UPJOHN CO. 23 March, 1966 [24 March, 1965], No. 12857/66. Heading C2U. [Also in Division A5] The invention comprises compounds of the formulµ wherein R, R 1 and R 2 each represent hydrogen or methyl, W is in which R 3 is hydrogen or the acyl radical of a C 1 -C 16 hydrocarbon carboxylic acid, R 4 is hydrogen or C 1 -C 4 hydrocarbon radical, X is Y is hydrogen or fluorine; and Z is compounds of the formulµ and the corresponding 17-keto compounds wherein R, R 1 , R 2 and R 3 are as defined above, compounds of the formulµ and a process that comprises treating a 6α-(2<SP>1</SP>- hydroxyethyl)-androst-4-ene-3-one with a sulphonic acid halide and subjecting the 6α-(2<SP>1</SP>- sulphonyloxyethyl)-androst-4-en-3-one so obtained to treatment with a strong base to produce the corresponding spiro-[androst-4-ene-6, 1<SP>1</SP>-cyclopropane]-3-one. If desired the 17#- hydroxy compounds may be acylated to form the 17#-acylates, the 3-keto compounds subjected to reduction to form the 3#-hydroxy compounds, the 11# hydroxy compound oxidized to form the corresponding 11-keto compounds and/or acylation may be effected to produce the corresponding 3#-acylate, 17#- acylate or 3#,17#-diacylate. Ring A saturation may be effected with hydrogen and palladized charcoal, and reduction of the 3-keto group with alkali metal borohydride. Oxidation may be effected with chromic acid, an N- haloamide or N-haloimide. The 3-tetrahydropyranyl ethers are obtained by treating a 3- hydroxy-17-acyloxy compound with dihydropyran in the presence of a Lewis acid and then if desired hydrolysing to produce the 17- hydroxy compound which in turn may be oxidized to form a 17-keto compound. The latter products may be hydrolysed in 3-position and the 3(3-hydroxy compounds so produced oxidized to the corresponding 3-keto compounds. The 17α - alkyl - 17# - hydroxy compounds are obtained by treating the corresponding 17-keto compounds with a Grignard reagent and if desired may be acylated to form the corresponding 17a-alkyl-17#-acyloxy compounds. #<SP>1</SP>'<SP>4</SP>-compounds are obtained from the corresponding #<SP>4</SP>-compounds by dehydrogenation, e.g. by fermentation or chemically as with Se02. The 2-hydroxymethylene products are obtained from the 2-unsubstituted compounds by treatment with an alkyl formate and sodium hydride in an inert atmosphere and if desired are treated with a lower alkanol in the presence of an acidic agent to give the corresponding 2-alkoxymethylene derivative.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US44252565A | 1965-03-24 | 1965-03-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1142484A true GB1142484A (en) | 1969-02-05 |
Family
ID=23757139
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB39137/68A Expired GB1142485A (en) | 1965-03-24 | 1966-03-23 | Improvements in or relating to steroids and the manufacture thereof |
GB12857/66A Expired GB1142484A (en) | 1965-03-24 | 1966-03-23 | Improvements in or relating to steroids and the manufacture thereof |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB39137/68A Expired GB1142485A (en) | 1965-03-24 | 1966-03-23 | Improvements in or relating to steroids and the manufacture thereof |
Country Status (6)
Country | Link |
---|---|
US (1) | US3600412A (en) |
CH (1) | CH481082A (en) |
DE (1) | DE1593610A1 (en) |
GB (2) | GB1142485A (en) |
IL (1) | IL25298A (en) |
NL (1) | NL6603861A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5319115A (en) * | 1987-08-25 | 1994-06-07 | Cocensys Inc. | Method for making 3α-hydroxy, 3β-substituted-pregnanes |
-
1965
- 1965-03-24 US US442525A patent/US3600412A/en not_active Expired - Lifetime
-
1966
- 1966-03-03 IL IL25298A patent/IL25298A/en unknown
- 1966-03-11 CH CH350066A patent/CH481082A/en not_active IP Right Cessation
- 1966-03-15 DE DE19661593610 patent/DE1593610A1/en active Pending
- 1966-03-23 GB GB39137/68A patent/GB1142485A/en not_active Expired
- 1966-03-23 GB GB12857/66A patent/GB1142484A/en not_active Expired
- 1966-03-24 NL NL6603861A patent/NL6603861A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
DE1593610A1 (en) | 1970-12-03 |
US3600412A (en) | 1971-08-17 |
GB1142485A (en) | 1969-02-05 |
NL6603861A (en) | 1966-09-26 |
CH481082A (en) | 1969-11-15 |
IL25298A (en) | 1970-08-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1512258A (en) | 18-methyl-19-nor-20-keto-pregnanes and process for their manufacture | |
GB1142484A (en) | Improvements in or relating to steroids and the manufacture thereof | |
GB1147803A (en) | Improvements in or relating to novel steroids and the manufacture thereof | |
GB1037162A (en) | Improvements in or relating to 19-oxo-androstane compounds and derivatives thereof | |
GB1146992A (en) | Improvements in or relating to novel steroids and the manufacture thereof | |
GB1472300A (en) | Process for the manufacture of a delta4-3-ketosteroid-17- propiolactone and of intermediates for such a lactone | |
GB1343975A (en) | 16beta-difluoromethyl and 16-fifluoromethylene steroids and processes for their preparation | |
GB1352865A (en) | Process for ethynylating 17-keto-steroids | |
GB1070113A (en) | Improvements in or relating to 17ª-(aliphatic hydrocarbonoxy) and 17ª-(substituted aliphatic hydrocarbonoxy) estrane derivatives | |
GB1051599A (en) | ||
GB893145A (en) | Improvements in or relating to steroids and the manufacture thereof | |
GB979037A (en) | New 6-alkyl-steroids | |
GB1337893A (en) | 4,5-secosteroids and a process for the manufacture thereof | |
GB1185381A (en) | 05,16beta-Methylene Steroids of the 19-Nor-Androstane Series and Process for their Manufacture | |
GB1235742A (en) | 01beta-METHYL-19-NORPREGNENE COMPOUNDS | |
GB1045474A (en) | 8ª‰-methyl-11ª‰-hydroxysteroids and their preparation | |
Akhtar et al. | Synthesis of rings A and B of strophanthidin | |
GB978540A (en) | Improvements in or relating to the production of 16ª-alkylthio-17-oxo-steroids | |
GB966099A (en) | Novel cyclopentanophenanthrene compounds and a process for the production thereof | |
GB1027268A (en) | New methyl-androstenes and process for their manufacture | |
GB1189475A (en) | 08-Alkylated-17alpha-(2-Alkynyl)estra-1,3,5(10)-Triene,3,17beta-Diols, Ethers and Esters Thereof | |
ES262796A1 (en) | New steroid compounds and their production | |
GB1235642A (en) | A new oestratriol and a process for its manufacture | |
GB1260398A (en) | NEW 18-METHYL-5alpha-H-ANDROSTANES | |
GB1184287A (en) | A process for the manufacture of Steroids of the Androstane Series |